Compound and organic light-emitting device including the same

ABSTRACT

The present disclosure relates to a compound represented by Formula 1 and an organic light-emitting device including the same. 
     
       
         
         
             
             
         
       
     
     The compound represented by Formula 1 has excellent stability and is suitable as an electron transporting material. An organic light-emitting device using the compound of Formula 1 may have high efficiency, low voltage, high luminance, and long lifespan.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2014-0170821, filed on Dec. 2, 2014, in the KoreanIntellectual Property Office, the disclosure of which is incorporatedherein in its entirety by reference.

BACKGROUND

1. Field

One or more aspects of embodiments of the present invention relate to acompound and an organic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices thathave wide viewing angles, high contrast ratios, and short responsetimes. In addition, OLEDs exhibit excellent luminance, low drivingvoltage, and quick response speed characteristics, and producefull-color images.

An organic light-emitting device may have a structure including an anodedisposed on a substrate, a hole transport layer, an emission layer, anelectron transport layer, and a cathode which are sequentially stackedon the anode in the stated order. Here, the hole transport layer, theemission layer, and the electron transport layer may be organic thinfilms formed of organic compounds.

The operating principle of an organic light-emitting device having theabove-described structure is as follows:

When a voltage is applied between the anode and the cathode, holesprovided from the anode may move toward the emission layer through thehole transport layer, and electrodes provided from the cathode may movetoward the emission layer through the electron transport layer. Theholes and the electrons are then recombined in the emission layer toproduce excitons. These excitons change from an excited state to aground state to thereby generate light.

There is a need to develop a material that has improved electricstability, high charge transporting and/or light-emitting capability,high glass transition temperature, and capability to prevent or reducecrystallization, as compared to an organic material of the related art.

SUMMARY

One or more aspects of embodiments of the present invention include acompound that is suitable as an electron transporting material and hasexcellent electric characteristics, high charge transporting andlight-emitting capability, high glass transition temperature, and/orhigh capability to prevent or substantially reduce crystallization. Anorganic light-emitting device including the compound may have highefficiency, low voltage, high luminance, and/or long lifespan.

Additional aspects of embodiments of the present invention will be setforth in part in the description which follows and, in part, will beapparent from the description, or may be learned by practice of thepresented embodiments.

According to one or more exemplary embodiments, a compound isrepresented by Formula 1:

In Formula 1,

R₁ to R₈ and Ar₁ to Ar₄ are each independently selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇);

where at least one selected from Ar₁ to Ar₄ is represented by Formula1-a:

In Formula 1-a,

R₁₁ is the same as defined in connection with R₁ to R₈;

m is an integer selected from 1 to 7; and

* indicates a binding site.

In Formulae 1 and 1-a, at least one of the substituents of thesubstituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀ alkoxy group,substituted C₃-C₁₀ cycloalkyl group, substituted C₂-C₁₀ heterocycloalkylgroup, substituted C₃-C₁₀ cycloalkenyl group, substituted C₂-C₁₀heterocycloalkenyl group, substituted C₆-C₆₀ aryl group, substitutedC₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthio group, substitutedC₁-C₆₀ heteroaryl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatic condensedheteropolycyclic group is selected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

where Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ are eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

According to one or more exemplary embodiments, an organiclight-emitting device includes: a first electrode; a second electrodefacing the first electrode; and an organic layer between the firstelectrode and the second electrode, wherein the organic layer includesan emission layer and the compound represented by Formula 1.

According to one or more exemplary embodiments, a flat panel displayapparatus may include the organic light-emitting device wherein a firstelectrode is electrically connected to a source electrode or drainelectrode of a thin film transistor.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the exemplary embodiments,taken in conjunction with the accompanying drawing which is a schematicview of an organic light-emitting device according to one or moreembodiments of the present invention.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawing, wherein like referencenumerals refer to like elements throughout. In this regard, the presentexemplary embodiments may have different forms and should not beconstrued as being limited to the descriptions set forth herein.Accordingly, the exemplary embodiments are merely described below, byreferring to the drawing, to explain aspects of the present description.As used herein, the term “and/or” includes any and all combinations ofone or more of the associated listed items. Expressions such as “atleast one of”, when preceding a list of elements, modify the entire listof elements and do not modify the individual elements of the list.Further, the use of “may” when describing embodiments of the presentinvention refers to “one or more embodiments of the present invention.”

In addition, as used herein, the terms “use,” “using,” and “used” may beconsidered synonymous with the terms “utilize,” “utilizing,” and“utilized,” respectively. Also, the term “exemplary” is intended torefer to an example or illustration.

As used herein, the term “substantially,” “about,” and similar terms areused as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art.

Also, any numerical range recited herein is intended to include allsub-ranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein. All suchranges are intended to be inherently described in this specificationsuch that amending to expressly recite any such subranges would complywith the requirements of 35 U.S.C. §1 12, first paragraph, and 35 U.S.C.§132(a).

According to one or more exemplary embodiments, a compound isrepresented by Formula 1:

In Formula 1,

R₁ to R₈ and Ar₁ to Ar₄ may be each independently selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇);

where at least one selected from Ar₁ to Ar₄ may be represented byFormula 1-a:

In Formula 1-a,

R₁₁ may be the same as defined in connection with R₁ to R₈;

m may be an integer selected from 1 to 7; and

* indicates a binding site.

In Formulae 1 and 1-a, at least one of the substituents of thesubstituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀ alkoxy group,substituted C₃-C₁₀ cycloalkyl group, substituted C₂-C₁₀ heterocycloalkylgroup, substituted C₃-C₁₀ cycloalkenyl group, substituted C₂-C₁₀heterocycloalkenyl group, substituted C₆-C₆₀ aryl group, substitutedC₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthio group, substitutedC₁-C₆₀ heteroaryl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

where Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

Compounds represented by Formula 1 and including a condensed ringstructure may have a high glass transition temperature (Tg) or a highmelting point, due to the presence of a condensed ring. Therefore,during emission, an organic light-emitting device may have improved heatresistance to Joule heating generated in an organic layer of the organiclight-emitting device, between the layers included in the organic layer,and between the organic layer and a metal electrode, and an improvedresistance to a high temperature. Thus, an organic light-emitting devicemanufactured using the compound represented by Formula 1 may retain highdurability during storing and driving.

In addition, Formula 1-a has a phenanthrofuran structure in whichphenanthrene structure is condensed with a furan structure, so thatπ-electrons in the overall structure are delocalized and lone pairs ofoxygen (O) are capable to partially provide excess electrons.

Accordingly, π→π* transition and n→π* transition may occur easily due toa phenanthrofuran structure connected to an amine group as well as thepyrene structure enriched with π-electrons that is positioned in thecenter of Formula 1.

Based on this principle, ultimately, molecular extinction coefficient inthe structure of Formula 1 may increase. Such an increase of themolecular extinction coefficient may lead to increase of luminousefficiency of the molecule, and thus, the compound represented byFormula 1 may have an improved luminous efficiency compared to otherknown and/or commonly used pyrene derivatives.

Accordingly, when the compound represented by Formula 1 is used as adopant in an emission layer in an organic light-emitting device, theorganic light-emitting device may have high efficiency.

In some embodiments, when a compound represented by Formula 4 (describedbelow) is used as a host in the emission layer together with thecompound of Formula 1 (used as a dopant), the organic light-emittingdevice may have an excellent efficiency.

Substituents of Formula 1 will be described in more detail below.

In some embodiments, among Ar₁ to Ar₄ in Formula 1, substituents otherthan Formula 1-a may be each independently selected from a substitutedor unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In some embodiments, in Formula 1, R₁ to R₈ may be each independentlyselected from a hydrogen, a deuterium, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₆-C₆₀ aryl group,and —Si(Q₃)(Q₄)(Q₅), where Q₃ to Q₅ are as defined above.

In some embodiments, among Ar₁ to Ar₄ in Formula 1, substituents otherthan Formula 1-a may be each independently represented by any one ofFormulae 2a to 2d:

In Formulae 2a to 2d, Z₁ may be selected from a hydrogen atom, adeuterium, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₆-C₂₀ aryl group, a substituted orunsubstituted C₁-C₂₀ heteroaryl group, a substituted or unsubstitutedC₆-C₂₀ condensed polycyclic group, a halogen group, a cyano group, anitro group, a hydroxyl group, and a carboxyl group;

H₁ may be selected from —O—, —S—, and —CR₅₁R₅₂—; p may be an integerselected from 1 to 9;

R₅₁ and R₅₂ may be the same as defined in connection with R₁ to R₈; and

* indicates a binding site.

In some embodiments, in Formula 1, R₂ and R₆ may be each independentlyselected from a hydrogen, a deuterium, a C₁-C₂₀ alkyl group, a C₆-C₂₀aryl group, and —Si(Q₄₁)(Q₄₂)(Q₄₃), where Q₄₁ to Q₄₃ may be eachindependently selected from a C₁-C₆₀ alkyl group and a C₆-C₆₀ arylgroup. In some embodiments, in Formula 1, R₂ and R₆ may be eachindependently selected from a hydrogen, a deuterium, a methyl group, at-butyl group, a phenyl group, and a tri-methyl silyl group.

In some embodiments, in Formula 1, R₁, R₃ to R₅, R₇, and R₈ may be eachindependently selected from a hydrogen and a deuterium.

In some embodiments, in Formula 1-a, R₁₁ may be selected from a hydrogenand a deuterium.

In some embodiments, the compound represented by Formula 1 may berepresented by any one of Formula 2 and 3:

Examples of the compound represented by Formula 1 include compoundsshown below, but embodiments of the present invention are not limitedthereto.

According to some exemplary embodiments, an organic light-emittingdevice may include, a first electrode; a second electrode; and anorganic layer between the first electrode and the second electrode,wherein the organic layer includes an emission layer and the compoundrepresented by Formula 1.

In some embodiments, the first electrode is an anode, the secondelectrode is a cathode, and the organic layer may include i) ahole-transport region between the first electrode and the emissionlayer, the hole-transport region including at least one selected from ahole injection layer, a hole-transport layer, and an electron blockinglayer and ii) an electron transport region between the emission layerand the second electrode, the electron transport region including atleast one selected from a hole blocking layer, an electron transportlayer, and an electron injection layer.

According to some embodiments, the emission layer may include thecompound according to one or more embodiments of the present invention.When the emission layer includes the compound, the compound may serve asa dopant.

As used herein, the term “organic layer” refers to a single layer and/ora plurality of layers disposed between the first electrode and thesecond electrode in an organic light-emitting device.

The drawing is a schematic view of an organic light-emitting device 10according to one or more embodiments of the present invention. Theorganic light-emitting device 10 includes a first electrode 110, anorganic layer 150, and a second electrode 190.

Hereinafter, a structure and a method of manufacturing the organiclight-emitting device according to some embodiments will be describedwith reference to the drawing.

Referring to the drawing, a substrate may be additionally positionedunder the first electrode 110 or on the second electrode 190. Thesubstrate may be a glass substrate or transparent plastic substrate,each with excellent mechanical strength, thermal stability,transparency, surface smoothness, ease of handling, and waterresistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode on the substrate. When thefirst electrode 110 is an anode, the material for the first electrodemay be selected from materials with a high work function such that theholes may be easily injected. The first electrode 110 may be areflective electrode, a semi-transmissive electrode, or a transmissiveelectrode. The material for the first electrode may be a transparent andhighly conductive material, and non-limiting examples of such materialinclude indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide(SnO₂), and zinc oxide (ZnO). When the first electrode 110 is asemi-transmissive electrode or a reflective electrode, as a material forforming the first electrode, at least one selected from magnesium (Mg),aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium(Mg—In), and magnesium-silver (Mg—Ag) may be used (utilized).

The first electrode 110 may have a single-layer structure, or amulti-layer structure including a plurality of layers. For example, thefirst electrode 110 may have a triple-layer structure of ITO/Ag/ITO, butembodiments of the present invention are not limited thereto.

The organic layer 150 is disposed on the first electrode 110. Theorganic layer 150 may include an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode and the emission layer, and an electrontransport region between the emission layer and the second electrode.

The hole transport region may include at least one selected from a holeinjection layer (HIL), a hole transport layer (HTL), a buffer layer, andan electron blocking layer (EBL), and the electron transport region mayinclude at least one selected from a hole blocking layer (HBL), anelectron transport layer (ETL), and an electron injection layer (EIL),but embodiments of the present invention are not limited thereto.

The hole transport region may have a single-layered structure formed ofa single material, a single-layered structure formed of a plurality ofdifferent materials, or a multi-layered structure having a plurality oflayers formed of a plurality of different materials.

For example, the hole transport region may have a single-layeredstructure formed of a plurality of different materials, or a structureof hole injection layer/hole transport layer, a structure of holeinjection layer/hole transport layer/buffer layer, a structure of holeinjection layer/buffer layer, a structure of hole transport layer/bufferlayer, or a structure of hole injection layer/hole transportlayer/electron blocking layer, where the layers of each structure aresequentially stacked from the first electrode 110 in the stated order,but embodiments of the present invention are not limited thereto.

When the hole transport region includes a hole injection layer, the holeinjection layer may be formed on the first electrode 110 by using(utilizing) one or more suitable methods, such as vacuum-deposition,spin coating, casting, Langmuir-Blodgett (LB) method, ink-jet printing,laser-printing, and/or laser-induced thermal imaging (LITI).

When the hole injection layer is formed by vacuum-deposition, forexample, the vacuum-deposition may be performed at a depositiontemperature of about 100° C. to about 500° C., at a vacuum degree ofabout 10⁻⁸ Torr to about 10⁻³ Torr, and at a vacuum-deposition rate in arange of about 0.01 Å/sec to about 100 Å/sec, depending on the compoundfor forming the hole injection layer, and the structure of the holeinjection layer to be formed.

When a hole injection layer is formed by spin coating, the spin coatingmay be performed at a coating rate of about 2000 rpm to about 5000 rpm,and at a temperature of about 80° C. to 200° C., depending on thecompound for forming the hole injection layer, and the structure of thehole injection layer to be formed.

When the hole transport region includes a hole transport layer, the holetransport layer may be formed on the first electrode 110 or the holeinjection layer by using one or more suitable methods, such asvacuum-deposition, spin coating, casting, LB method, ink-jet printing,laser-printing, and/or LITI. When the hole transport layer is formed byvacuum-deposition and/or spin coating, conditions for vacuum-depositionand coating may be similar to to the above-described vacuum-depositionand coating conditions for forming the hole injection layer.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, a spiro-TPD, a spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonicacid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compoundrepresented by Formula 201 below, and a compound represented by Formula202 below:

In Formulae 201 and 202,

L₂₀₁ and L₂₀₅ may be each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group;

xa1 to xa4 may be each independently selected from 0, 1, 2, and 3; and

xa5 may be selected from 1, 2, 3, 4, and 5;

R₂₀₁ to R₂₀₄ may be each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In some embodiments, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may be each independently selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group;

xa1 to xa4 may be each independently selected from 0, 1, and 2;

xa5 may be selected from 1, 2, and 3;

R₂₀₁ to R₂₀₄ may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, an azulenyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group; but embodiments of the present invention are notlimited thereto.

The compound represented by Formula 201 may be represented by Formula201A:

In some embodiments, the compound represented by Formula 201 may berepresented by Formula 201A-1, but embodiments of the present inventionare not limited thereto:

In some embodiments, the compound represented by Formula 202 may berepresented by Formula 202A, but embodiments of the present inventionare not limited thereto:

In Formulae 201A, 201A-1, and 202A, L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, andR₂₀₂ to R₂₀₄ may be understood by referring to the descriptions providedherein, and R₂₁₁ may be the same as defined in connection with R₂₀₃; andR₂₁₃ to R₂₁₆ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group.

In some embodiments, in Formulae 201A-1 and 202A,

L₂₀₁ to L₂₀₃ may be each independently selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group;

xa1 to xa3 may be each independently selected from 0 and 1;

R₂₀₃, R₂₁₁ and R₂₁₂ may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, aphenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group;

R₂₁₃ and R₂₁₄ may be each independently selected from:

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group;

R₂₁₅ and R₂₁₆ may be each independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group;

and xa5 may be selected from 1 and 2.

In Formulae 201A and 201A-1, R₂₁₃ and R₂₁₄ may link to each other so asto form a saturated ring or an unsaturated ring.

The compound represented by Formula 201 and the compound represented byFormula 202 may each independently include Compounds HT1 to HT20, butembodiments of the present invention are not limited thereto.

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1000 Å. When thehole transport region includes a hole injection layer and a holetransport layer, the thickness of the hole injection layer may be in arange of about 100 Å to about 10,000 Å, for example, about 100 Å toabout 9,950 Å, or about 100 Å to about 1000 Å, and the thickness of thehole transport layer may be in a range of about 50 Å to about 2000 Å,and for example, about 100 Å to about 1500 Å. When the thicknesses ofthe hole transport region, the hole injection layer, and the holetransport layer are within any of these ranges, excellent hole transportcharacteristics may be obtained without a substantial increase indriving voltage.

The hole transport region may further include, in addition to thematerials mentioned above, a charge-generating material to improveconductive properties. The charge-generating material may behomogeneously or non-homogeneously dispersed throughout the holetransport region.

The charge-generating material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but is not limited thereto.Non-limiting examples of the p-dopant include quinone derivatives suchas tetracyanoquinonedimethane (TCNQ) and/or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ);metal oxides such as a tungsten oxide and/or a molybdenum oxide; andCompound HT-D1 illustrated below.

The hole transport region may further include, in addition to the holeinjection layer and the hole transport layer, at least one selected froma buffer layer and an electron blocking layer. Since the buffer layermay compensate for an optical resonance distance according to awavelength of light emitted from the emission layer, light-emissionefficiency of the resulting organic light-emitting device may beimproved. As a material included in the buffer layer, materials that areincluded in the hole transport region may be used (utilized). In someembodiments, the electron blocking layer prevents or substantiallyreduces the injection of electrons from the electron transport region.

An emission layer may be formed on the first electrode 110 or the holetransport region by using one or more suitable methods, such asvacuum-deposition, spin coating, casting, LB method, ink-jet printing,laser-printing, and/or LITI. When the emission layer is formed byvacuum-deposition and/or spin coating, deposition and coating conditionsfor the emission layer may be similar to the deposition and coatingconditions for the hole injection layer.

When the organic light-emitting device 10 is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to a sub pixel. Alternatively, the emission layer may have astacked structure of a red emission layer, a green emission layer, and ablue emission layer, or may include a red-light emission material, agreen-light emission material, and a blue-light emission material, whichare mixed with each other in a single layer, to emit white light.

According to some embodiments, the emission layer may further include acompound represented by Formula 4.

In Formula 4, R₂₁ to R₃₆ may be each independently selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇);

at least one of the substituents of the substituted C₁-C₆₀ alkyl group,substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group,substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group,substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group maybe selected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

where Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

In some embodiments, the compound represented by Formula 4 may serve asa host.

In some embodiments, in Formula 4, R₂₅, R₂₇, R₃₁, R₃₂, and R₃₃ may beeach independently selected from a hydrogen, a deuterium, a cyano group,a substituted or unsubstituted C₁-C₆₀ alkyl group, —Si(Q₃)(Q₄)(Q₅)(where Q₃ to Q₅ are as defined above), and Formulae 3a to 3c:

In Formulae 3a to 3c, Z₁ may be selected from a hydrogen atom, adeuterium, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₆-C₂₀ aryl group, a substituted orunsubstituted C₁-C₂₀ heteroaryl group, a substituted or unsubstitutedC₆-C₂₀ condensed polycyclic group, a halogen group, a cyano group, anitro group, a hydroxyl group, and a carboxyl group;

H₁ may be selected from —O—, —S—, —CR₅₁R₅₂—, and —NR₅₃—; p may be aninteger selected from 1 to 7; and * indicates a binding site;

R₅₁ and R₅₃ may be the same as defined in connection with R₂₁ to R₃₆described above; and

optionally, R₅₁ and R₅₂ may be linked to each other to form a ring.

In some embodiments, in Formula 4, R₂₁ to R₂₄, R₂₆, R₂₈ to R₃₀, and R₃₄to R₃₆ may be each independently selected from a hydrogen and adeuterium.

In some embodiments, the emission layer may include the compoundrepresented by Formula 1 as a fluorescent or phosphorescent dopant andthe compound represented by Formula 4 as a fluorescent or phosphorescenthost.

The compound represented by Formula 4 may be, for example, representedby any one of compounds below, but is not limited thereto:

The emission layer may include any suitable host and dopant commonlyknown to those of skill in the art, as well as the compound representedby Formula 1 and compound represented by Formula 4.

The host may include at least one selected from TPBi, TBADN, ADN(herein, also known as “DNA”), CBP, CDBP, and TCP:

In some embodiments, the host may include at least one selected fromCompounds H43 to H49 below, but is not limited thereto:

The dopant may further include at least one selected from a suitablefluorescent dopant and a phosphorescent dopant.

The phosphorescent dopant may include an organometallic complexrepresented by Formula 401 below:

In Formula 401,

M may be selected from iridium (Ir), platinum (Pt), osmium (Os),titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium(Tb), and thulium (Tm);

X₄₀₁ to X₄₀₄ may be each independently nitrogen or carbon;

A₄₀₁ and A₄₀₂ rings may be each independently selected from asubstituted or unsubstituted benzene, a substituted or unsubstitutednaphthalene, a substituted or unsubstituted fluorene, a substituted orunsubstituted spiro-fluorene, a substituted or unsubstituted indene, asubstituted or unsubstituted pyrrole, a substituted or unsubstitutedthiophene, a substituted or unsubstituted furan, a substituted orunsubstituted imidazole, a substituted or unsubstituted pyrazole, asubstituted or unsubstituted thiazole, a substituted or unsubstitutedisothiazole, a substituted or unsubstituted oxazole, a substituted orunsubstituted isoxazole, a substituted or unsubstituted pyridine, asubstituted or unsubstituted pyrazine, a substituted or unsubstitutedpyrimidine, a substituted or unsubstituted pyridazine, a substituted orunsubstituted quinoline, a substituted or unsubstituted isoquinoline, asubstituted or unsubstituted benzoquinoline, a substituted orunsubstituted quinoxaline, a substituted or unsubstituted quinazoline, asubstituted or unsubstituted carbazole, a substituted or unsubstitutedbenzoimidazole, a substituted or unsubstituted benzofuran, a substitutedor unsubstituted benzothiophene, a substituted or unsubstitutedisobenzothiophene, a substituted or unsubstituted benzoxazole, asubstituted or unsubstituted isobenzoxazole, a substituted orunsubstituted triazole, a substituted or unsubstituted oxadiazole, asubstituted or unsubstituted triazine, a substituted or unsubstituteddibenzofuran, and a substituted or unsubstituted dibenzothiophene;

at least one of substituents of the substituted benzene, substitutednaphthalene, substituted fluorene, substituted spiro-fluorene,substituted indene, substituted pyrrole, substituted thiophene,substituted furan, substituted imidazole, substituted pyrazole,substituted thiazole, substituted isothiazole, substituted oxazole,substituted isoxazole, substituted pyridine, substituted pyrazine,substituted pyrimidine, substituted pyridazine, substituted quinoline,substituted isoquinoline, substituted benzoquinoline, substitutedquinoxaline, substituted quinazoline, substituted carbazole, substitutedbenzoimidazole, substituted benzofuran, substituted benzothiophene,substituted isobenzothiophene, substituted benzoxazole, substitutedisobenzoxazole, substituted triazole, substituted oxadiazole,substituted triazine, substituted dibenzofuran, and substituteddibenzothiophene may be selected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₄₀₁)(Q₄₀₂), —Si(Q₄₀₃)(Q₄₀₄)(Q₄₀₅),and —B(Q₄₀₆)(Q₄₀₇),

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₁-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₄₁₁)(Q₄₁₂), —Si(Q₄₁₃)(Q₄₁₄)(Q₄₁₅),and —B(Q₄₁₆)(Q₄₁₇), and

—N(Q₄₂₁)(Q₄₂₂), —Si(Q₄₂₃)(Q₄₂₄)(Q₄₂₅), and —B(Q₄₂₆)(Q₄₂₇);

where Q₄₀₁ to Q₄₀₇, Q₄₁₁ to Q₄₁₇, and Q₄₂₁ to Q₄₂₇, are eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

L₄₀₁ may be an organic ligand;

xc1 may be selected from 1, 2, and 3; and

xc2 may be selected from 0, 1, 2, and 3.

L₄₀₁ may be any suitable monovalent, divalent, or trivalent organicligand. For example, L₄₀₁ may be selected from a halogen ligand (forexample, Cl⁻ or F⁻), a diketone ligand (for example, acetylacetonate,1,3-diphenyl-1,3-propanedionate, 2,2,6,6-tetramethyl-3,5-heptanedionate,and/or hexafluoroacetonate), a carboxylic acid ligand (for example,picolinate, dimethyl-3-pyrazolecarboxylate, and/or benzoate), a carbonmonooxide ligand, an isonitrile ligand, a cyano ligand, and aphosphorous ligand (for example, phosphine, or phosphate), butembodiments of the present invention are not limited thereto.

When A₄₀₁ in Formula 401 has a plurality of substituents, two or more ofthe plurality of substituents of A₄₀₁ may bind to each other to form asaturated or unsaturated ring.

When A₄₀₂ in Formula 401 has a plurality of substituents, two or more ofthe plurality of substituents of A₄₀₂ may bind to each other to form asaturated or unsaturated ring.

When xc1 in Formula 401 is two or more, a plurality of ligands

in Formula 401 may be identical to or different from each other. InFormula 401, when xc1 is 2 or more, A₄₀₁ and/or A₄₀₂ of one ligand maybe respectively linked to A₄₀₁ and/or A₄₀₂ of an adjacent ligand,directly (e.g., via a single bond) or connected via a linking group (forexample, a C₁-C₅ alkylene group, —N(R′)— (wherein R′ is a C₁-C₁₀ alkylgroup or a C₆-C₂₀ aryl group), and/or —C(═O)—).

The fluorescent dopant may include at least one selected from DPVBi,BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T as well as the compoundrepresented by Formula 1.

An amount of the dopant in the emission layer may be, in general, in arange of about 0.01 parts by weight to about 15 parts by weight based on100 parts by weight of the host, but the amount of the dopant is notlimited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer (ETL), and an electroninjection layer, but embodiments of the present invention are notlimited thereto.

For example, the electron transport region may have a structure ofelectron transport layer/electron injection layer or a structure of holeblocking layer/electron transport layer/electron injection layer, wherethe layers of each structure are sequentially stacked from the emissionlayer in the stated order, but the structure of the electron transportregion is not limited thereto.

The electron transport region may include a hole blocking layer. Whenthe emission layer includes a phosphorescent dopant, the hole blockinglayer may be formed to prevent or substantially reduce the diffusion ofexcitons or holes into an electron transport layer.

When the electron transport region includes a hole blocking layer, thehole blocking layer may be formed on the emission layer by using one ormore suitable methods, such as vacuum-deposition, spin coating, casting,LB method, ink-jet printing, laser-printing, and/or LITI. When the holeblocking layer is formed by vacuum-deposition and/or spin coating, thedeposition and coating conditions for the hole blocking layer may besimilar to the deposition and coating conditions for the hole injectionlayer.

The hole blocking layer may include, for example, at least one selectedfrom BCP and Bphen, but is not limited thereto.

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1000 Å, for example, about 30 Å to about 300 Å. When thethickness of the hole blocking layer is within this range, excellenthole blocking characteristics may be obtained without a substantialincrease in driving voltage.

The electron transport region may include an electron transport layer.The electron transport layer may be formed on the emission layer or thehole blocking layer by using one or more suitable methods, such asvacuum deposition, spin coating, casting, LB method, ink-jet printing,laser-printing, and/or LITI. When the electron transport layer is formedby using vacuum deposition and/or spin coating, vacuum deposition andcoating conditions for the electron transport layer may be similar tothe vacuum deposition and coating conditions for the hole injectionlayer.

In some embodiments, the organic layer 150 of the organic light-emittingdevice includes an electron transport region between the emission layerand the second electrode 190. The electron transport region may includeat least one selected from an electron transport layer and an electroninjection layer, but is not limited thereto.

The electron transport layer may include at least one selected from BCP,Bphen, Alq₃, BAlq, TAZ, and NTAZ.

In some embodiments, the electron transport layer may include at leastone compound selected from a compound represented by Formula 601 and acompound represented by Formula 602 illustrated below: Formula 601

Ar₆₀₁-[(L₆₀₁)_(xe1)-E₆₀₁]_(xe2).

In Formula 601,

Ar₆₀₁ may be selected from:

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene;

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene,naphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃),

where Q₃₀₁ to Q₃₀₃ may be each independently selected from a hydrogen, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₆-C₆₀ aryl group, and aC₁-C₆₀ heteroaryl group;

L₆₀₁ may be the same as defined in connection with L₂₀₁;

E₆₀₁ may be selected from:

a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group; and

a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group;

xe1 may be selected from 0, 1, 2, and 3; and

xe2 may be selected from 1, 2, 3, and 4.

In Formula 602,

X₆₁₁ may be N or C-(L₆₁₁)_(xe611)-R₆₁₁, X₆₁₂ may be N orC-(L₆₁₂)_(xe612)-R₆₁₂, X₆₁₃ may be N or C-(L₆₁₃)_(xe613)-R₆₁₃, and atleast one selected from X₆₁₁ to X₆₁₃ may be N;

L₆₁₁ to L₆₁₆ may be each independently the same as defined in connectionwith L₂₀₁ provided herein;

R₆₁₁ to R₆₁₆ may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group;

xe611 to xe616 may be each independently selected from 0, 1, 2, and 3.

The compound represented by Formula 601 and the compound represented byFormula 602 may each independently be selected from Compounds ET1 toET15 illustrated below:

A thickness of the electron transport layer may be in a range of about100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When thethickness of the electron transport layer is within this range,excellent electron transport characteristics may be obtained without asubstantial increase in driving voltage.

The electron transport layer may further include a metal-containingmaterial in addition to the materials described above.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) orET-D2:

The electron transport region may include an electron injection layerthat facilitates electron injection from the second electrode 190.

The electron injection layer may be formed on the electron transportlayer by using one or more suitable methods, such as vacuum-deposition,spin coating, casting, LB method, ink-jet printing, laser-printing,and/or LITI. When the electron injection layer is formed by vacuumdeposition and/or spin coating, vacuum deposition and coating conditionsfor the electron injection layer may be similar to the vacuum-depositionand coating conditions for the hole injection layer.

The electron injection layer may include at least one selected from LiF,NaCl, CsF, Li₂O, BaO, and LiQ.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within this range,excellent electron injection characteristics may be obtained without asubstantial increase in driving voltage.

The second electrode 190 is positioned on the organic layer 150. Thesecond electrode 190 may be a cathode that is an electron injectionelectrode, and in this regard, a material for forming the secondelectrode 190 may be a material having a low work function, for example,a metal, an alloy, an electrically conductive compound, or a mixturethereof. Non-limiting examples of the material for forming the secondelectrode 190 include lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag). In some embodiments, the material for formingthe second electrode 190 may be ITO or IZO. The second electrode 190 maybe a reflective electrode, a semi-transmissive electrode, or atransmissive electrode.

Hereinbefore, the organic light-emitting device has been described withreference to the drawing, but embodiments of the present invention arenot limited thereto.

Hereinafter, definitions of substituents used herein will be presented(the number of carbon numbers used to restrict a substituent is notlimited, and does not limit properties of the substituent, and unlessstated otherwise, the definition of the substituent is consistent with ageneral definition thereof).

A C₁-C₆₀ alkyl group used herein refers to a linear or branchedaliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms inthe main carbon chain, and non-limiting examples thereof include amethyl group, an ethyl group, a propyl group, an iso-butyl group, asec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group,and a hexyl group. A C₁-C₆₀ alkylene group used herein refers to adivalent group having the same structure as the C₁-C₆₀ alkyl group.

A C₁-C₆₀ alkoxy group used herein refers to a monovalent grouprepresented by —OA₁₀₁ (where A₁₀₁ is the C₁-C₆₀ alkyl group), andnon-limiting examples thereof include a methoxy group, an ethoxy groupand an isopropyloxy group.

A C₂-C₆₀ alkenyl group used herein refers to a hydrocarbon group havingat least one carbon-carbon double bond at one or more positions along acarbon chain of the C₂-C₆₀ alkyl group (e.g., in the middle or at eitherterminal end of the C₂-C₆₀ alkyl group), and non-limiting examplesthereof include an ethenyl group, a propenyl group, and a butenyl group.A C₂-C₆₀ alkenylene group used herein refers to a divalent group havingthe same structure as the C₂-C₆₀ alkenyl group.

A C₂-C₆₀ alkynyl group used herein refers to a hydrocarbon group havingat least one carbon-carbon triple bond at one or more positions along acarbon chain of the C₂-C₆₀ alkyl group (e.g., in the middle or at eitherterminal end of the C₂-C₆₀ alkyl group), and non-limiting examplesthereof include an ethynyl group and a propynyl group. A C₂-C₆₀alkynylene group used herein refers to a divalent group having the samestructure as the C₂-C₆₀ alkynyl group.

A C₃-C₁₀ cycloalkyl group used herein refers to a monovalent monocyclicsaturated hydrocarbon group including 3 to 10 carbon atoms asring-forming atoms, and non-limiting examples thereof include acyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexylgroup, and a cycloheptyl group. A C₃-C₁₀ cycloalkylene group used hereinrefers to a divalent group having the same structure as the C₃-C₁₀cycloalkyl group.

A C₁-C₁₀ heterocycloalkyl group used herein refers to a monovalentmonocyclic group including at least one hetero atom selected from N, O,P, and S as a ring-forming atom and 1 to 10 carbon atoms as theremaining ring-forming atoms. Non-limiting examples thereof include atetrahydrofuranyl group and a tetrahydrothiophenyl group. A C₁-C₁₀heterocycloalkylene group used herein refers to a divalent group havingthe same structure as the C₁-C₁₀ heterocycloalkyl group.

A C₃-C₁₀ cycloalkenyl group used herein refers to a monovalentmonocyclic group that has 3 to 10 carbon atoms as ring-forming atoms andat least one double bond in its ring, and is not aromatic. Non-limitingexamples thereof include a cyclopentenyl group, a cyclohexenyl group,and a cycloheptenyl group. A C₃-C₁₀ cycloalkenylene group used hereinrefers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

A C₁-C₁₀ heterocycloalkenyl group used herein refers to a monovalentmonocyclic group including at least one hetero atom selected from N, O,P, and S as a ring-forming atom, 1 to 10 carbon atoms as the remainingring-forming atoms, and at least one double bond in its ring.Non-limiting examples of the C₁-C₁₀ heterocycloalkenyl group include a2,3-hydrofuranyl group and a 2,3-hydrothiophenyl group. A C₁-C₁₀heterocycloalkenylene group used herein refers to a divalent grouphaving the same structure as the C₁-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group used herein refers to a monovalent group including acarbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group used herein refers to a divalent group including acarbocyclic aromatic system having 6 to 60 carbon atoms. Non-limitingexamples of the C₆-C₆₀ aryl group include a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, anda chrysenyl group. When the C₆-C₆₀ aryl group and/or the C₆-C₆₀ arylenegroup each include a plurality of rings, the rings may be fused to eachother.

A C₁-C₆₀ heteroaryl group used herein refers to a monovalent grouphaving a carbocyclic aromatic system including at least one hetero atomselected from N, O, P, and S as a ring-forming atom and 1 to 60 carbonatoms as the remaining ring-forming atoms. A C₁-C₆₀ heteroarylene groupused herein refers to a divalent group having a carbocyclic aromaticsystem including at least one hetero atom selected from N, O, P, and Sas a ring-forming atom and 1 to 60 carbon atoms as the remainingring-forming atoms. Non-limiting examples of the C₁-C₆₀ heteroaryl groupinclude a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group. When the C₁-C₆₀ heteroaryl group and/or the C₁-C₆₀heteroarylene group each include a plurality of rings, the rings may befused to each other.

A C₆-C₆₀ aryloxy group used herein refers to a group represented by—OA₁₀₂ (where A₁₀₂ is the C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthiogroup used herein refers to a group represented by —SA₁₀₃ (where A₁₀₃ isthe C₆-C₆₀ aryl group).

A monovalent non-aromatic condensed polycyclic group used herein refersto a monovalent group that has two or more rings condensed to eachother, only carbon atoms as ring forming atoms (for example, the numberof carbon atoms may be in a range of 6 to 60 as in, for example, aC₆-C₂₀ condensed polycyclic group), wherein the molecular structure as awhole is non-aromatic. A non-limiting example of the monovalentnon-aromatic condensed polycyclic group is a fluorenyl group. A divalentnon-aromatic condensed polycyclic group used herein refers to a divalentgroup having the same structure as the monovalent non-aromatic condensedpolycyclic group.

A monovalent non-aromatic condensed heteropolycyclic group used hereinrefers to a monovalent group that has two or more rings condensed toeach other, has a hetero atom selected from N, O P, and S as aring-forming atom, and carbon atoms as the remaining ring-forming atoms(for example, the number of carbon atoms may be in a range of 2 to 60),wherein the molecular structure as a whole is non-aromatic. Anon-limiting example of the monovalent non-aromatic condensedheteropolycyclic group is a carbazolyl group. A divalent non-aromaticcondensed heteropolycyclic group used herein refers to a divalent grouphaving the same structure as the monovalent non-aromatic condensedheteropolycyclic group.

At least one of substituents of the substituted C₃-C₁₀ cycloalkylenegroup, substituted C₁-C₁₀ heterocycloalkylene group, substituted C₃-C₁₀cycloalkenylene group, substituted C₁-C₁₀ heterocycloalkenylene group,substituted C₆-C₆₀ arylene group, substituted C₁-C₆₀ heteroarylenegroup, substituted divalent non-aromatic condensed polycyclic group,substituted divalent non-aromatic condensed heteropolycyclic group,substituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀ alkoxy group,substituted C₃-C₁₀ cycloalkyl group, substituted C₁-C₁₀ heterocycloalkylgroup, substituted C₃-C₁₀ cycloalkenyl group, substituted C₁-C₁₀heterocycloalkenyl group, substituted C₆-C₆₀ aryl group, substitutedC₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthio group, substitutedC₁-C₆₀ heteroaryl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

where Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

In some embodiments, at least one substituent of the substituted C₃-C₁₀cycloalkylene group, substituted C₁-C₁₀ heterocycloalkylene group,substituted C₃-C₁₀ cycloalkenylene group, substituted C₁-C₁₀heterocycloalkenylene group, substituted C₆-C₆₀ arylene group,substituted C₁-C₆₀ heteroarylene group, substituted divalentnon-aromatic condensed polycyclic group, substituted divalentnon-aromatic condensed heteropolycyclic group, substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₁-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group andsubstituted monovalent non-aromatic condensed heteropolycyclic group maybe selected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a pentalenyl group, an indenylgroup, a naphthyl group, an azulenyl group, a heptalenyl group, anindacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovalenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇);

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a pentalenyl group, an indenylgroup, a naphthyl group, an azulenyl group, a heptalenyl group, anindacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovalenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇),

where Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a thiadiazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group.

The organic light-emitting device according to one or more embodimentsof the present invention may be included in various types (kinds) offlat panel display apparatuses, for example, in a passive matrix organiclight-emitting display apparatus and/or an active matrix organiclight-emitting display apparatus. When the organic light-emitting deviceis included in an active matrix organic light-emitting displayapparatus, a first electrode disposed on a substrate is a pixelelectrode, and the first electrode may be electrically connected to asource electrode or drain electrode of a thin film transistor. Inaddition, the organic light-emitting device may be included in a flatpanel display apparatus that may display images on both sides.

Further, the organic layer of the organic light-emitting deviceaccording to the present embodiments may be formed by vacuum-depositingthe compound desribed above in connection with one or more embodimentsof the present invention and/or using (utilizing) a wet method in whichthe compound according to one or more embodiments of the presentinvention is prepared in the form of a solution, and then the solutionof the compound is used for coating.

“Ph” used herein refers to a phenyl group, “Me” refers to a methylgroup, “Et” refers to an ethyl group, and “ter-Bu” or “Bu^(t)” refers toa tert-butyl group.

Hereinafter, an organic light-emitting device according to one or moreembodiments will be described in detail with reference to SynthesisExamples and Examples. However, these examples are for illustrativepurposes only and are not intended to limit the scope of the presentinvention.

EXAMPLE Synthesis Example 1 Synthesis of Compound 8

Synthesis of Intermediate I-1

17.2 g (54.4 mmol) of 1-bromo-4-chloro-2-iodobenzene, 600 mg (2.7 mmol)of Pd(OAc)₂, 1.5 g (5.72 mmol) of PPh₃, and 1.1 g (5.77 mmol) of CuIwere dissolved in 375 ml (272 mmol) of triethylamine, and the resultingsolution was stirred at 60° C. for 12 hours under N₂ atmosphere. Oncethe reaction was complete, the result was allowed to cool down to roomtemperature. Then, an organic layer was extracted five times therefromby using each of water and diethyl ether. The obtained organic layer wasdried by using magnesium sulfate (MgSO₄). Then, a solvent was removedtherefrom by evaporation. The obtained residue was separated andpurified through a silica gel chromatography to thereby obtain 25.2 g(47.6 mmol) of Intermediate I-1 (yield: 87.5%). The obtained compoundwas identified by mass spectroscopy/fast atom bombardment (MS/FAB).

C11H12BrBrSi cal. 287.65, found 287.68.

Synthesis of Intermediate I-2

25.2 g (47.6 mmol) of Intermediate I-1 was dissolved in 500 ml oftetrahydrofuran (THF), and was stirred at −78° C. for 10 minutes underN₂ atmosphere. Then, 19 ml of 2.5 M n-BuLi was slowly added dropwise byusing a dropping funnel, and the resulting solution was stirred foradditional 30 minutes. Then, 4.95 g (52.4 mmol) of trimethyl borate wasslowly added dropwise by using a dropping funnel, and the solution wasadditionally stirred for three hours at room temperature. Then, 300 mlof 1M hydro-chloride solution was added thereto. An organic layer wasextracted once therefrom, and was extracted three times additionallytherefrom by using each of water and diethyl ether. The obtained organiclayer was dried by using MgSO₄. A solvent was removed therefrom byevaporation. The obtained residue was separated and purified through asilica gel chromatography to obtain 8.64 g (34.2 mmol) of IntermediateI-2 (yield: 72%). The obtained compound was identified by MS/FAB.

C11H14BClO2Si cal. 252.58, found 252.60.

Synthesis of Intermediate I-3

24.8 g (20.0 mmol) of 2-methoxyphenol and 3 g (60.0 mmol) of a pyridinewere dissolved in 60 mL of dichloromethane. Then, 6.0 g (22 mmol) oftriflic anhydride were slowly added thereto at 0° C., and the resultingproduct was allowed to cool down to room temperature and was thenstirred for 2 hours. An organic layer was extracted three timestherefrom by adding each of 30 mL of water and 50 mL of dichloromethane.The obtained organic layer was dried by using MgSO₄. Then, a solvent wasremoved therefrom by evaporation. The obtained residue was separated andpurified through a silica gel chromatography to thereby obtain 47.1 g(18.4 mmol) of Intermediate I-3 (yield: 92%). The obtained compound wasidentified by MS/FAB.

C8H7F3O4S cal. 256.19, found 256.22.

Synthesis of Intermediate I-4

2.52 g (10 mmol) of Intermediate I-2, 2.82 g (11 mmol) of IntermediateI-3, 1.16 g (7.5 mmol) of Pd(PPh₃)₄, and 4.15 g (30 mmol) of K₂CO₃ wereadded to a 200 ml of mixture of THF/H₂O (at a volume ratio of 9:1), andthe resulting solution was stirred at 80° C. for 12 hours. The mixturewas allowed to cool down to room temperature. Then, an organic layer wasextracted three times therefrom by using each of 50 mL of water and 50mL of diethyl ether. The obtained organic layer was dried by usingMgSO₄. Then, a solvent was removed therefrom by evaporation. Theobtained residue was separated and purified through a silica gelchromatography to obtain 2.36 g (7.5 mmol) of Intermediate I-4 (yield:75%). The obtained compound was identified by MS/FAB.

C18H19ClOSi cal. 314.88, found 314.90.

Synthesis of Intermediate I-5

2.36 g (7.5 mmol) of Intermediate I-4 and 3.11 g (22.5 mmol) of K₂CO₃were dissolved in 200 ml of MeOH/CH₂Cl₂ (at a volume ratio of 2:1), andthe resulting solution was stirred at room temperature for 1 hour. Oncethe reaction was complete, the obtained compound was filtered by using afilter. An organic solvent was removed from the filtrate by evaporation.Then, an organic layer was extracted therefrom two times by using waterand dichloromethane. Then, the resulting organic layer was dried byusing MgSO₄. The residue obtained by evaporating the solvent wasseparated and purified through a silica get chromatography to therebyobtain 1.61 g (6.63 mmol) of Intermediate I-5 (yield: 88.5%). Theobtained compound was identified by MS/FAB.

C15H11ClO cal. 242.70, found 242.75.

Synthesis of Intermediate I-6

1.61 g (6.63 mmol) of Intermediate I-5 was dissolved in 100 mL ofmethylene chloride, and was stirred for 30 minutes while maintaining 0°C. in an ice bath. Then, 4.33 g (7.02 mmol) of iodine chloride was addedthereto and the resulting solution was stirred for 30 minutes. Once thereaction was complete, an organic layer was extracted therefrom fivetimes by using 100 mL of water, and ethylacetate. Then, the obtainedorganic layer was dried by using MgSO₄, and a solvent was removedtherefrom by evaporation. The obtained residue was recrystallized with amixture solution of methylene chloride and n-hexane to thereby obtain1.34 g (5.54 mmol) of Intermediate I-6 (yield: 83.5%). The obtainedcompound was identified by MS/FAB. C15H11ClO cal. 242.70, found 242.73.

Synthesis of Intermediate I-7

1.34 g (5.54 mmol) of Intermediate I-6 and 4.67 g (27.8 mmol) of sodiumethanethiolate were dissolved in 100 mL of dimethylformamide (DMF), andthe resulting solution was stirred at 130° C. 4 hours later, the resultwas allowed to cool down to room temperature. Then, an organic layer wasextracted six times therefrom by using water and ethyl acetate. Theobtained organic layer was dried by using MgSO₄. Then, a solvent wasremoved therefrom by evaporation. The obtained residue was separated andpurified through a silica gel chromatography to thereby obtain 1.19 g(5.21 mmol) of Intermediate I-7 (yield: 94%). The obtained compound wasidentified by MS/FAB.

C14H9ClO cal. 228.67, found 228.70.

Synthesis of Intermediate I-8

1.19 g (5.21 mmol) of Intermediate I-7 and 2.24 g (15.6 mmol) of copper(I) oxide were added to 100 mL of nitro-benzene and the resultingsolution was stirred at 190° C. for 48 hours. The result was allowed tocool down to room temperature, and then, an organic layer was extractedfour times therefrom by using 50 mL of water and 50 mL of diethyl ether.The obtained organic layer was dried by using MgSO₄. Then, a solvent wasremoved therefrom by evaporation. The obtained residue was separated andpurified through a silica gel chromatography to thereby obtain 0.93 g(4.11 mmol) of Intermediate I-8 (yield: 79.3%). The obtained compoundwas identified by MS/FAB.

C14H7ClO cal. 226.65, found 226.71.

Synthesis of Intermediate I-A

0.93 g (4.11 mmol) of Intermediate I-8, 0.28 g (3.00 mmol) of aniline,0.03 g (0.03 mmol) of Pd₂(dba)₃, 0.003 g (0.03 mmol) of PtBu₃, and 0.86g (9 mmol) of NaOtBu were dissolved in 30 mL of toluene, and then, theresulting solution was stirred at 85° C. for 4 hours. After allowing theresult to cool down to room temperature, an organic layer was extractedthree times therefrom by using 30 mL of water and 30 mL of diethylether. The obtained organic layer was dried by using MgSO₄. A solventwas removed therefrom by evaporation. The obtained residue was separatedand purified through a silica gel chromatography to obtain 0.61 g (2.16mmol) of Intermediate I-A (yield: 72%). The obtained compound wasidentified by MS/FAB.

C20H13NO cal. 283.33, found 283.35.

Synthesis of Intermediate 8-1

3.6 g (20.0 mmol) of 1,6-dibromopyrene, 0.38 g (2.0 mmol) of CuI, and6.7 g (120.0 mmol) of KOH were dissolved in 100 mL of mixture solutionof toluene/PEG400/H₂O (at a volume ratio of 5:4:1) under N₂ atmosphere,and the resulting solution was stirred for 8 hours while heating up tomaintain 110° C. The result was allowed to cool down to roomtemperature, and then, 10 mL of 1N HCl was added thereto to adjust pH tobe in a range of about 2 to about 3. Then, an organic layer wasextracted three times therefrom by using 60 mL of ethyl acetate. Theobtained organic layer was dried by using MgSO₄. Then, a solvent wasremoved therefrom by evaporation. The obtained residue was separated andpurified through a silica gel chromatography to thereby obtain 3.8 g(12.8 mmol) of Intermediate 8-1 (yield: 64%). The obtained compound wasidentified by MS/FAB.

C16H9BrO cal. 297.15, found 297.21.

Synthesis of Intermediate 8-2

2.97 g (10.0 mmol) of Intermediate 8-1, 3.11 g (11.0 mmol) ofIntermediate I-A, 0.18 g (0.2 mmol) of Pd₂(dba)₃, 0.04 g (0.2 mmol) ofPtBu₃, and 1.9 g (20.0 mmol) of NaOtBu were dissolved in 30 mL oftoluene, and then the resulting solution was stirred at 85° C. for 4hours. After allowing the result to cool down to room temperature, anorganic layer was extracted three times therefrom by using 30 mL ofwater and 30 mL of diethyl ether. The obtained organic layer was driedby using MgSO₄. A solvent was removed therefrom by evaporation. Theobtained residue was separated and purified through a silica gelchromatography to obtain 4.68 g (7.2 mmol) of Intermediate 8-2 (yield:72%). The obtained compound was identified by MS/FAB.

C36H21NO2 cal. 499.56, found 499.61.

Synthesis of Intermediate 8-3

4.27 g (6.77 mmol) of Intermediate 8-3 (yield: 94%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-3 except that Intermediate 8-2 was used instead of 2-methoxyphenol.The obtained compound was identified by MS/FAB.

C37H20F3NO4S cal. 631.62, found 631.66.

Synthesis of Compound 8

4.28 g (6.77 mmol) of Intermediate 8-3, 1.84 g (7.11 mmol) of Compound8-A, 0.06 g (0.07 mmol) of Pd₂(dba)₃, 0.01 g (0.07 mmol) of PtBu₃, and0.97 g (10.2 mmol) of NaOtBu were dissolved in 30 mL of toluene, andthen the resulting solution was stirred at 85° C. for 4 hours. Afterallowing the result to cool down to room temperature, an organic layerwas extracted three times therefrom by using 30 mL of water and 30 mL ofdiethyl ether. The obtained organic layer was dried by using MgSO₄.Then, a solvent was removed therefrom by evaporation. The obtainedresidue was separated and purified through a silica gel chromatographyto thereby obtain 4.31 g (5.82 mmol) of Compound 8 (yield: 86%). Theobtained compound was identified by MS/FAB and ₁H NMR.

C55H36N2O cal. 740.90, found 740.92.

¹H NMR (400 MHz, CDCl₃) ** 7.93-7.48 (m, 16H), 7.13-6.51 (m, 15H),6.29-6.27 (m, 2H), 1.86 (s, 3H)

Synthesis Example 2 Synthesis of Compound 14

Synthesis of Intermediate I-9

12.8 g (45 mmol) of Intermediate I-9 (yield: 86%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-1 except that 2-bromo-4-chloro-1-iodobenzene was used instead of1-bromo-4-chloro-2-iodobenzene. The obtained compound was identified byMS/FAB.

C11H12BrClSi cal. 287.66, found 287.69.

Synthesis of Intermediate I-10

8.51 g (33.8 mmol) of Intermediate I-10 (yield: 75%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-2 except that Intermediate I-9 was used instead of Intermediate I-1.The obtained compound was identified by MS/FAB.

C11H14BClO2Si cal. 252.57, found 252.62.

Synthesis of Intermediate I-11

6.58 g (20.9 mmol) of Intermediate I-11 (yield: 62%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-4 except that Intermediate I-10 was used instead of Intermediate I-2.The obtained compound was identified by MS/FAB.

C18H19ClOSi cal. 314.88, found 314.96.

Synthesis of Intermediate I-12

4.60 g (19.0 mmol) of Intermediate I-12 (yield: 91%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-5 except that Intermediate I-11 was used instead of Intermediate I-4.The obtained compound was identified by MS/FAB.

C15H11ClO cal. 242.70, found 242.73.

Synthesis of Intermediate I-13

3.63 g (15.0 mmol) of Intermediate I-13 (yield: 79%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-6 except that Intermediate I-12 was used instead of Intermediate I-5.The obtained compound was identified by MS/FAB.

C15H11ClO cal. 242.70, found 242.74.

Synthesis of Intermediate I-14

2.91 g (12.8 mmol) of Intermediate I-14 (yield: 85%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-7 except that Intermediate I-13 was used instead of Intermediate I-6.The obtained compound was identified by MS/FAB.

C14H9ClO cal. 228.67, found 228.72.

Synthesis of Intermediate I-15

2.35 g (10.4 mmol) of Intermediate I-15 (yield: 81.1%) was obtained inthe same (or substantially the same) manner as in Synthesis ofIntermediate I-8 except that Intermediate I-14 was used instead ofIntermediate I-7. The obtained compound was identified by MS/FAB.

C14H7ClO cal. 226.66, found 226.68.

Synthesis of Intermediate I-B

2.53 g (8.94 mmol) of Intermediate I-B (yield: 86%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-A except that Intermediate I-15 was used instead of Intermediate I-8.The obtained compound was identified by MS/FAB.

C20H13NO cal. 283.33, found 283.37.

Synthesis of Intermediate 14-1

2.35 g (5.8 mmol) of Intermediate 14-1 (yield: 79.5%) was obtained inthe same (or substantially the same) manner as in Synthesis ofIntermediate 8-2 except that Intermediate I-B was used instead ofIntermediate I-A. The obtained compound was identified by MS/FAB.

C36H21NO2 cal. 499.57, found 499.60.

Synthesis of Intermediate 14-2

3.44 g (5.45 mmol) of Intermediate 14-2 (yield: 94%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-3 except that Intermediate 14-1 was used instead of 2-methoxyphenol.The obtained compound was identified by MS/FAB.

C37H20F3NO4S cal. 631.62, found 631.65.

Synthesis of Compound 14

3.17 g (3.87 mmol) of Compound 14 (yield: 71%) was obtained in the same(or substantially the same) manner as in Synthesis of Compound 8 exceptthat Intermediate 14-2 was used instead of Intermediate 8-3, andCompound 14-A was used instead of Compound 8-A. The obtained compoundwas identified by MS/FAB and ₁H NMR.

C60H36N2O2 cal. 816.96, found 816.99.

¹H NMR (400 MHz, CDCl₃) □□ 7.98-7.42 (m, 22H), 7.42-6.85 (m, 11H),6.63-6.61 (m, 1H), 6.29-6.27 (m, 2H)

Synthesis Example 3 Synthesis of Compound 21

Synthesis of Intermediate I-16

10.3 g (36 mmol) of Intermediate I-16 (yield: 82%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-1 except that 1-bromo-3-chloro-2-iodobenzene was used instead of1-bromo-4-chloro-2-iodobenzene.

The obtained compound was identified by MS/FAB.

C11H12BrClSi cal. 287.66, found 287.69.

Synthesis of Intermediate I-17

7.17 g (28.4 mmol) of Intermediate I-17 (yield: 79%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-2 except that Intermediate I-16 was used instead of Intermediate I-1.The obtained compound was identified by MS/FAB.

C11H14BClO2Si cal. 252.57, found 252.62.

Synthesis of Intermediate I-18

5.89 g (18.7 mmol) of Intermediate I-18 (yield: 66%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-4 except that Intermediate I-17 was used instead of Intermediate I-2.The obtained compound was identified by MS/FAB.

C18H19ClOSi cal. 314.88, found 314.96.

Synthesis of Intermediate I-19

4.30 g (17.8 mmol) of Intermediate I-19 (yield: 95%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-5 except that Intermediate I-18 was used instead of Intermediate I-4.The obtained compound was identified by MS/FAB.

C15H11ClO cal. 242.70, found 242.73.

Synthesis of Intermediate I-20

2.97 g (12.3 mmol) of Intermediate I-20 (yield: 69%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-6 except that Intermediate I-19 was used instead of Intermediate I-5.The obtained compound was identified by MS/FAB.

C15H11ClO cal. 242.70, found 242.74.

Synthesis of Intermediate I-21

2.53 g (11.1 mmol) of Intermediate I-21 (yield: 90%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-7 except that Intermediate I-20 was used instead of Intermediate I-6.The obtained compound was identified by MS/FAB.

C14H9ClO cal. 228.67, found 228.72.

Synthesis of Intermediate I-22

1.91 g (8.44 mmol) of Intermediate I-22 (yield: 76%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-8 except that Intermediate I-21 was used instead of Intermediate I-7.The obtained compound was identified by MS/FAB.

C14H7ClO cal. 226.66, found 226.68.

Synthesis of Intermediate I-C

1.94 g (6.84 mmol) of Intermediate I-C (yield: 81%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-A except that Intermediate I-22 was used instead of Intermediate I-8.The obtained compound was identified by MS/FAB.

C20H13NO cal. 283.33, found 283.37.

Synthesis of Intermediate 21-1

2.50 g (5.0 mmol) of Intermediate 21-1 (yield: 77%) was obtained in thesame (or substantially the same) manner as in Synthesis of Intermediate8-2 except that Intermediate I-C was used instead of Intermediate I-A.The obtained compound was identified by MS/FAB.

C36H21NO2 cal. 499.57, found 499.60.

Synthesis of Intermediate 21-2

2.97 g (4.70 mmol) of Intermediate 21-2 (yield: 94%) was obtained in thesame (or substantially the same) manner as in Synthesis of IntermediateI-3 except that Intermediate 21-1 was used instead of 2-methoxyphenol.The obtained compound was identified by MS/FAB.

C37H20F3NO4S cal. 631.62, found 631.65.

Synthesis of Compound 21

2.74 g (3.34 mmol) of Compound 21 (yield: 71%) was obtained in the same(or substantially the same) manner as in Synthesis of Compound 8 exceptthat Intermediate 21-2 was used instead of Intermediate 8-3, andCompound 21-A was used instead of Compound 8-A. The obtained compoundwas identified by MS/FAB and ₁H NMR.

C60H37FN2O cal. 820.96, found 820.99.

¹H NMR (400 MHz, CDCl₃) □□ 7.84-7.32 (m, 24H), 7.11-7.00 (m, 6H),6.82-6.80 (m, 1H), 6.59-6.55 (m, 2H), 6.17-6.12 (m, 4H)

Synthesis Example 4 Synthesis of Compound 31

Synthesis of Intermediate 31-1

7.2 g (20.0 mmol) of 1,6-dibromopyrene was dissolved in 60 mL of THF,and was cooled to −78° C. 48.0 mL of n-BuLi (2.5M in hexane) was slowlyadded thereto, and the resulting solution was heated up to −30° C., andthen was stirred. 1 hour later, the result was cooled to −78° C. 7.5 mLof iodomethane was slowly added thereto, and the resulting solution wasstirred at room temperature for 4 hours. An organic layer was extractedthree times therefrom by using 60 mL of water and 60 mL of diethylether. The obtained organic layer was dried by using MgSO₄. Then, asolvent was removed therefrom by evaporation. The obtained residue wasseparated and purified through a silica gel chromatography to therebyobtain 2.99 g (13 mmol) of Intermediate 31-1 (yield: 65%). The obtainedcompound was identified by MS/FAB.

C18H14 cal. 230.31, found 230.35.

Synthesis of Intermediate 31-2

2.9 g (12.6 mmol) of Intermediate 31-1 was dissolved in 30 mL of amixture solution of diethyl ether/methanol (at a volume ratio of 2.5:1).3.8 mL of HBr (33 wt % in AcOH) was slowly added thereto at 0° C., andthe resulting solution was stirred for 30 minutes. 1.73 mL ofhydrogenperoxide (30 wt % in H₂O) was slowly added to the resultingsolution at the same temperature, and the obtained solution was stirredat room temperature for 8 hours. Once the reaction was complete, anorganic layer was extracted three times therefrom by using 30 mL ofwater and 30 mL of diethyl ether. The obtained organic layer was driedby using MgSO₄. Then, a solvent was removed therefrom by evaporation.The obtained residue was separated and purified through a silica gelchromatography to thereby obtain 3.58 g (11.6 mmol) of Intermediate 31-2(yield: 92%). The obtained compound was identified by MS/FAB.

C18H13Br cal. 309.21, found 309.26.

Synthesis of Intermediate 31-3

3.5 g (11.3 mmol) of Intermediate 31-2 was dissolved in 30 mL ofdichloromethane, and then, a solution of 0.85 g (12.4 mmol) of NaNO₂dissolved in 10 mL of trifluoroacetic acid was slowly added thereto, andthe resulting solution was stirred at 0° C. for 30 minutes. 10 mL oftriethylamine was then added to the resulting solution in order tocomplete the reaction. Then, the formed solid was filtered. Then, anorganic layer was extracted three times therefrom by using 40 mL ofwater and 30 mL of dichloromethane. The obtained organic layer was driedby using MgSO₄. Then, a solvent was removed therefrom by evaporation.The obtained residue was separated and purified through a silica gelchromatography to thereby obtain 2.88 g (8.14 mmol) of Intermediate 31-3(yield: 72%). The obtained compound was identified by MS/FAB.

C18H12BrNO2 cal. 354.20, found 354.24.

Synthesis of Intermediate 31-4

2.86 g (8.1 mmol) of Intermediate 31-3, 2.75 g (9.72 mmol) ofIntermediate I-B, 0.15 g (0.17 mmol) of Pd₂(dba)₃, 0.03 g (0.17 mmol) ofPtBu₃, and 1.2 g (12.5 mmol) of NaOtBu were dissolved in 30 mL oftoluene, and then the resulting solution was stirred at 85° C. for 4hours. After allowing the result to cool down to room temperature, anorganic layer was extracted three times therefrom by using each of 30 mLof water and 30 mL of diethyl ether. The obtained organic layer wasdried by using MgSO₄. Then, a solvent was removed therefrom byevaporation. The obtained residue was separated and purified through asilica gel chromatography to thereby obtain 3.38 g (6.08 mmol) ofIntermediate 31-4 (yield: 75%). The obtained compound was identified byMS/FAB.

C38H24N2O3 cal. 556.62, found 556.66.

Synthesis of Intermediate 31-5

3.38 g (6.08 mmol) of Intermediate 31-4 was dissolved in 20 mL of amixture solution of dichloromethane/methanol (at a volume ratio of 1:1).Then, 0.5 g of Pd/C was added thereto, and the resulting solution wasstirred in a reaction vessel while introducing hydrogen gas into thereaction vessel at 1 atm for 3 hours. Once the reaction was complete,the resulting solution was filtrated by using a celite. The obtainedorganic layer was dried by using MgSO₄. Then, a solvent was removedtherefrom by evaporation. The obtained residue was separated andpurified through a silica gel chromatography to thereby obtain 2.85 g(5.41 mmol) of Intermediate 31-5 (yield: 89%). The obtained compound wasidentified by MS/FAB.

C38H26N2O3 cal. 526.63, found 526.67.

Synthesis of Intermediate 31-6

2.85 g (5.41 mmol) of Intermediate 31-5 was dissolved in 15 mL ofacetonitrile. Then, 16 mL of 1N HCl was added slowly thereto at 0° C.The resulting solution was stirred at the same temperature for 30minutes. NaNO₂ 0.92 g (13.3 mmol) was slowly added thereto, and theobtained solution was stirred for additional 30 minutes. 8 g (48 mmol)of potassium iodide (KI) was added to the resulting solution, and theobtained reaction mixture was stirred for 2 hours. 20 mL of saturatedNaHCO₃ solution was added to the reaction mixture. Then, an organiclayer was extracted three times therefrom by using 30 mL of ethylacetate. The obtained organic layer was dried by using MgSO₄. Then, asolvent was removed therefrom by evaporation. The obtained residue wasseparated and purified through a silica gel chromatography to therebyobtain 2.10 g (3.30 mmol) of Intermediate 31-6 (yield: 61%). Theobtained compound was identified by MS/FAB.

C38H24INO cal. 637.52, found 637.55.

Synthesis of Compound 31

1.97 g (3.1 mmol) of Intermediate 31-6, 0.88 g (3.6 mmol) of Compound31-A, 0.05 g (0.06 mmol) of Pd₂(dba)₃, 0.01 g (0.06 mmol) of PtBu₃, and0.44 g (4.6 mmol) of NaOtBu were dissolved in 20 mL of toluene, and thenthe resulting solution was stirred at 85° C. for 4 hours. After allowingthe result to cool down to room temperature, an organic layer wasextracted three times therefrom by using each of 20 mL of water and 20mL of diethyl ether. The obtained organic layer was dried by usingMgSO₄. Then, a solvent was removed therefrom by evaporation. Theobtained residue was separated and purified through a silica gelchromatography to thereby obtain 1.94 g (2.57 mmol) of Compound 31(yield: 83%). The obtained compound was identified by MS/FAB and ₁H NMR.

C38H24INO cal. 754.93, found 754.96.

¹H NMR (400 MHz, CDCl₃) 8.09 (d, 1H), 7.98 (d, 1H), 7.78-7.45 (m, 13H),7.25-7.00 (m, 9H), 6.82 (d, 1H), 6.63-6.55 (m, 3H), 6.28-6.26 (m, 2H),6.04-6.02 (m, 2H), 2.57 (s, 6H)

Synthesis Example 5 Synthesis of Compound 42

2.65 g (3.04 mmol) of Compound 42 (yield: 79%) was obtained in the same(or substantially the same) manner as in Synthesis of Compound 31 exceptthat

Compound 42-A was used instead of Compound 31-A. The obtained compoundwas identified by MS/FAB and ₁H NMR.

C65H46N2O cal. 871.09, found 871.14.

¹H NMR (400 MHz, CDCl₃) 8.00 (d, 1H), 7.97 (d, 1H), 7.78-7.70 (m, 6H),7.65-7.43 (m, 8H), 7.36-7.30 (m, 2H), 7.21 (d, 1H), 7.15-6.93 (m, 9H),6.63-6.55 (m, 3H), 6.30-6.24 (m, 3H), 6.06 (s, 1H), 2.57 (s, 6H), 1.61(s, 6H)

Synthesis Example 6 Synthesis of Compound 48

3.10 g (3.46 mmol) of Compound 48 (yield: 71%) was obtained in the same(or substantially the same) manner as in Synthesis of Compound 8 exceptthat Intermediate I-D was used instead of Intermediate I-A, and Compound48-A was used instead of Compound 8-A. The obtained compound wasidentified by MS/FAB and ₁H NMR.

C66H41FN20 cal. 897.06, found 897.12.

¹H NMR (400 MHz, CDCl₃) 7.91-7.30 (m, 28H), 7.13-6.89 (m, 8H), 6.76-6.61(m, 3H), 6.10-6.08 (m, 2H)

Synthesis Example 7 Synthesis of Compound 55

2.50 g (3.02 mmol) of Compound 55 (yield: 78%) was obtained in the same(or substantially the same) manner as in Synthesis of Compound 14 exceptthat Compound 55-A was used instead of Compound 14-A. The obtainedcompound was identified by MS/FAB and ₁H NMR.

C62H38N2O cal. 826.99, found 827.03.

¹H NMR (400 MHz, CDCl₃) 8.46 (d, 1H), 7.98-7.45 (m, 22H), 7.16-6.67 (m,10H), 6.63-6.60 (m, 2H), 6.29-6.27 (m, 2H)

Synthesis Example 8 Synthesis of Compound 60

Synthesis of Intermediate 60-1

2.9 g (12.6 mmol) of Compound 31-1 was dissolved in 30 mL of a mixturesolution of diethyl ether/methanol (at a volume ratio of 2.5:1). 7.6 mLof HBr (33 wt % in AcOH) was slowly added thereto at 0° C., and theresulting solution was stirred for 30 minutes. 3.4 mL ofhydrogenperoxide (30 wt % in H₂O) was slowly added to the resultingsolution at the same temperature, and the mixture was stirred at roomtemperature for 8 hours. Once the reaction was complete, an organiclayer was extracted three times therefrom by using each of 30 mL ofwater and 30 mL of diethyl ether. The obtained organic layer was driedby using MgSO₄. Then, a solvent was removed therefrom by evaporation.The obtained residue was separated and purified through a silica gelchromatography to thereby obtain 4.11 g (10.6 mmol) of Intermediate 60-1(yield: 84%). The obtained compound was identified by MS/FAB.

C18H12Br2 cal. 388.10, found 388.22.

Synthesis of Compound 60

2.08 g (2.62 mmol) of Compound 60 (yield: 81%) was obtained in the same(or substantially the same) manner as in Synthesis of Intermediate 31-4except that Intermediate 60-1 was used instead of Intermediate 31-3. Theobtained compound was identified by MS/FAB and ₁H NMR.

C58H36N2O2 cal. 792.93, found 792.95.

¹H NMR (400 MHz, CDCl₃) 8.11-8.09 (m, 2H), 7.76-7.49 (m, 14H), 7.23-7.21(m, 2H), 7.06-7.00 (m, 6H), 6.63-6.60 (m, 2H), 6.28-6.20 (m, 4H), 2.57(m, 6H),

Synthesis Example 8 Synthesis of Compound 72

3.11 g (3.39 mmol) of Compound 72 (yield: 72%) was obtained in the same(or substantially the same) manner as in Synthesis of Intermediate 31-4except that 1,6-dibromopyrene was used instead of Intermediate 31-3, andIntermediate I-D was used instead of Intermediate I-B. The obtainedcompound was identified by MS/FAB and ₁H NMR.

C68H40N2O2 cal. 917.08, found 917.13.

¹H NMR (400 MHz, CDCl₃) 7.96-7.94 (m, 2H), 7.78-7.30 (m, 26H), 7.20-7.15(m, 6H), 7.01-6.97 (m, 6H)

The following Compounds were prepared and identified by ¹H NMR andMS/FAB. The results thereof are shown in Table 1.

Methods of synthesizing compounds other than Compounds shown in Table 1should be apparent to those skilled in the art by referring to thesynthesis pathways and raw materials described in Synthesis Examples 1to 8.

TABLE 1 MS/FAB Compound ¹H NMR (CDCl₃, 400 MHz) found calc. 1 δ =7.93-7.90 (m, 2H), 7.80-7.70 (m, 3H), 650.80 650.78 7.52-7.47 (m, 7H),7.14-7.02 (m, 8H), 6.71-6.61 (m, 4H), 6.29-6.27 (m, 2H), 6.14-6.10 (m,4H) 4 δ = 7.97 (d, 1H), 7.90 (d, 1H), 7.78-7.74 (m, 3H), 795.16 795.147.65-7.45 (m, 7H), 7.40-7.32 (m, 5H), 7.23-7.15 (m, 3H), 7.06-7.01 (m,2H), 6.65-6.62 (m, 1H), 6.56-6.50 (m, 5H), 6.20-6.12 (m, 2H), 0.24 (s,9H), 0.27 (s, 9H) 12 δ = 7.98-7.70 (m, 3H), 7.55-7.48 (m, 5H), 843.06843.04 7.35-7.07 (m, 22H), 6.53-6.50 (m, 2H), 6.32-6.29 (m, 3H),6.25-6.20 (m, 1H), 1.61 (s, 6H) 16 δ = 7.96-7.30 (m, 22H), 7.11-7.07 (m,8H), 820.97 820.96 6.71-6.65 (m, 3H), 6.29-6.25 (m, 2H), 6.08-6.05 (m,2H) 20 δ = 8.11-7.75 (m, 9H), 7.70-7.35 (m, 13H), 833.04 833.027.29-6.97 (m, 10H), 6.67-6.60 (m, 2H), 6.29-6.25 (m, 2H) 23 δ = 7.99 (d,1H), 7.85-7.75 (m, 5H), 7.66-7.39 (m, 816.99 816.96 17H), 7.30-6.82 (m,10H), 6.63-6.61 (m, 1H), 6.04-6.02 (m, 2H) 29 δ = 8.01-7.70 (m, 7H),7.48-7.45 (m, 2H), 7.32 (d, 1H), 772.29 772.29 7.05-7.00 (m, 8H), 6.83(d, 1H), 6.64-6.62 (m, 3H), 6.15-6.10 (m, 6H), 2.57 (s, 6H) 34 δ = 7.91(d, 1H), 7.85-7.68 (m, 4H), 7.60-7.43 (m, 799.07 799.06 11H), 7.40-7.37(m, 2H), 7.20-7.09 (m, 4H), 7.04-6.95 (m, 4H), 6.83 (d, 1H), 6.69-6.59(m, 4H), 6.04-6.02 (m, 2H), 0.24 (s, 9H) 38 δ = 8.32-8.30 (m, 2H),8.04-7.96 (m, 2H), 915.21 915.19 7.80-7.68 (m, 3H), 7.60-7.45 (m, 11H),7.34 (d, 1H), 7.20-7.11 (m, 3H), 7.06-6.97 (m, 7H), 6.82-6.79 (m, 2H),6.74-6.63 (m, 2H), 6.63-6.60 (m, 1H), 6.03-6.00 (m, 2H), 1.48 (s, 18H)40 δ = 7.93-7.70 (m, 5H), 7.52-7.39 (m, 13H), 751.90 751.88 7.16-7.00(m, 8H), 6.79-6.63 (m, 5H), 6.04-6.02 (m, 2H), 44 δ = 7.93-7.30 (m,22H), 7.07-7.00 (m, 5H), 863.10 863.04 6.74-6.52 (m, 5H), 6.10-6.08 (m,2H), 2.28 (s, 3H), 2.15 (s, 6H) 49 δ = 7.93-7.41 (m, 22H), 7.18-7.06 (m,7H), 802.99 802.97 6.80-6.69 (m, 5H), 6.27-6.20 (m, 4H) 62 δ = 8.45-8.43(m, 2H), 8.27-8.25 (m, 2H), 909.27 909.25 7.78-7.75 (m, 6H), 7.68-7.63(m, 4H), 7.48-7.46 (m, 2H), 7.23-7.21 (m, 2H), 7.09-7.02 (m, 6H),6.63-6.59 (m, 2H), 6.27-6.23 (m, 4H), 0.41 (s, 18H) 67 δ = 8.08-7.99 (m,6H), 7.64-7.58 (m, 6H), 917.10 917.08 7.50-7.43 (m, 12H), 7.18-7.04 (m,8H), 6.73-6.70 (m, 4H), 6.32-6.28 (m, 4H) 70 δ = 8.00-7.98 (m, 2H),7.90-7.84 (m, 2H), 881.07 881.04 7.78-7.71 (m, 7H), 7.67-7.54 (m, 6H),7.48-7.40 (m, 3H), 7.33-7.30 (m, 1H), 7.11-7.09 (m, 2H), 7.06-7.01 (m,4H), 6.67-6.59 (m, 2H), 6.46-6.44 (m, 1H), 6.29-6.27 (m, 2H), 1.61 (s,6H)

Example 1

A Corning 15 Ohms per square centimeter (Ω/cm₂) (1200 Å) ITO glasssubstrate was cut to a size of 50 millimeters (mm)×50 mm×0.7 mm,sonicated in isopropyl alcohol and pure water, for 5 minutes in eachsolvent, and cleaned by exposure to ultraviolet rays with ozone so as touse the glass substrate as an anode. Then, the obtained glass substratewas mounted in a vacuum-deposition apparatus.4,4′-Bis[N-phenyl-N-(9-phenylcarbazol-3-yl)amino]-1,1′-biphenyl(Compound 301) was first vacuum-deposited on the substrate as a holeinjection layer having a thickness of about 600 Å. Then, a holetransporting compound(N-[1,1′-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-amine(Compound 311)) was vacuum-deposited on the hole injection layer to forma hole transport layer having a thickness of about 300 Å.

9,10-di-naphthalene-2-yl-anthracene (ADN) as a blue fluorescent host,and

Compound 8 as a blue fluorescent dopant, were co-deposited at a weightratio of about 98:2 on the hole transport layer to form an emissionlayer having a thickness of about 300 Å.

Afterward, Alq₃ was vacuum-deposited on the emission layer to form anelectron transport layer having a thickness of about 300 Å. Then, LiF,an alkali metal halide, was vacuum-deposited on the electron transportlayer to form an electron injection layer having a thickness of about 10Å. Aluminum (Al) was vacuum-deposited on the electron injection layer toform a cathode having a thickness of about 3000 Å, thereby forming aLiF/Al electrode to complete the manufacture of an organiclight-emitting device.

Example 2

Organic light-emitting devices were manufactured in the same (orsubstantially the same) manner as in Example 1 except that Compound 14was used instead of Compound 8 to form an emission layer.

Example 3

Organic light-emitting devices were manufactured in the same (orsubstantially the same) manner as in Example 1 except that Compound 21was used instead of Compound 8 to form an emission layer.

Example 4

Organic light-emitting devices were manufactured in the same (orsubstantially the same) manner as in Example 1 except that Compound 31was used instead of Compound 8 to form an emission layer.

Example 5

Organic light-emitting devices were manufactured in the same (orsubstantially the same) manner as in Example 1 except that Compound 42was used instead of Compound 8 to form an emission layer.

Example 6

Organic light-emitting devices were manufactured in the same (orsubstantially the same) manner as in Example 1 except that Compound 48was used instead of Compound 8 to form an emission layer.

Example 7

Organic light-emitting devices were manufactured in the same (orsubstantially the same) manner as in Example 1 except that Compound 55was used instead of Compound 8 to form an emission layer.

Example 8

Organic light-emitting devices were manufactured in the same (orsubstantially the same) manner as in Example 1 except that Compound 60was used instead of Compound 8 to form an emission layer.

Example 9

Organic light-emitting devices were manufactured in the same (orsubstantially the same) manner as in Example 1 except that Compound 72was used instead of Compound 8 to form an emission layer.

Comparative Example 1

Organic light-emitting devices were manufactured in the same (orsubstantially the same) manner as in Example 1 except thatN,N,N′,N′-tetraphenyl-pyrene-1,6-diamine (TPD) was used as a dopantinstead of Compound 8.

The characteristics of organic light-emitting devices according toExamples 1 to 9 and Comparative Example 1 are shown in Table 2.

TABLE 2 Driving Current voltage density Luminance Efficiency EmissionHalf-life Dopant (V) (mA/cm²) (cd/m²) (cd/A) color (hr @100 mA/cm²)Example 1 Compound 8 6.64 50 3,105 6.21 blue 333 hr Example 2 Compound6.67 50 3,185 6.37 blue 342 hr 14 Example 3 Compound 6.70 50 3,200 6.40blue 338 hr 21 Example 4 Compound 6.62 50 3,210 6.42 blue 347 hr 31Example 5 Compound 6.71 50 3,230 6.46 blue 361 hr 42 Example 6 Compound6.72 50 3,165 6.33 blue 341 hr 48 Example 7 Compound 6.75 50 3,205 6.41blue 376 hr 55 Example 8 Compound 6.64 50 3,325 6.65 blue 383 hr 60Example 9 Compound 6.58 50 3,290 6.58 blue 365 hr 72 Comparative TPD6.96 50 2,730 5.46 blue 248 hr Example 1

Comparative Example 2

An organic emission layer was manufactured in the same (or substantiallythe same) manner as in Example 1 except that in forming an emissionlayer, Compound H9 represented by Formula 4 was used as a host insteadof ADN, and TPD was used as a dopant instead of Compound 8.

Example 10

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1 except that in forming anemission layer, Compound H9 represented by Formula 4 was used as a hostinstead of ADN.

Example 11

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 10 except that Compound 14was used instead of Compound 8 to form an emission layer.

Example 12

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 10 except that Compound 21was used instead of Compound 8 to form an emission layer.

Example 13

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 10 except that Compound 31was used instead of Compound 8 to form an emission layer.

Example 14

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 10 except that Compound 42was used instead of Compound 8 to form an emission layer.

Example 15

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 10 except that in formingan emission layer, Compound H45 was used as a host instead of CompoundH9, and Compound 14 was used as a dopant instead of Compound 8.

Example 16

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 15 except that Compound 21was used instead of Compound 14 to form an emission layer.

Example 17

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 15 except that Compound 31was used instead of Compound 14 to form an emission layer.

Example 18

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 15 except that Compound 42was used instead of Compound 14 to form an emission layer.

Example 19

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 15 except that Compound 48was used instead of Compound 14 to form an emission layer.

Example 20

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 15 except that Compound 55was used instead of Compound 14 to form an emission layer.

Example 21

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 15 except that Compound 60was used instead of Compound 14 to form an emission layer.

Example 22

An organic light-emitting device was manufactured in the same manner asin Example 10 except that in forming an emission layer, Compound H60 wasused as a host instead of Compound H9, and Compound 14 was used as adopant instead of Compound 8.

Example 23

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 22 except that Compound 21was used instead of Compound 14 to form an emission layer.

Example 24

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 22 except that Compound 42was used instead of Compound 14 to form an emission layer.

Example 25

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 22 except that Compound 55was used instead of Compound 14 to form an emission layer.

Example 26

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 22 except that Compound 60was used instead of Compound 14 to form an emission layer.

Example 27

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 22 except that Compound 72was used instead of Compound 14 to form an emission layer.

The characteristics of organic light-emitting devices according toExamples 10 to 27 and Comparative Examples 1 and 2 are shown in Table 3.

TABLE 3 Driving Current half- voltage density Luminance EfficiencyEmission life (hr Host Dopant (V) (mA/cm²) (cd/m²) (cd/A) color @100mA/cm²) Example 10 Compound Compound 8 6.54 50 3,275 6.55 blue 442 hr H9Example 11 Compound Compound 6.55 50 3,330 6.66 blue 456 hr H9 14Example 12 Compound Compound 6.61 50 3,370 6.74 blue 437 hr H9 21Example 13 Compound Compound 6.58 50 3,365 6.73 blue 479 hr H9 31Example 14 Compound Compound 6.57 50 3,375 6.75 blue 481 hr H9 42Example 15 Compound Compound 6.52 50 3,345 6.69 blue 467 hr H45 14Example 16 Compound Compound 6.58 50 3,365 6.73 blue 471 hr H45 21Example 17 Compound Compound 6.53 50 3,425 6.85 blue 478 hr H45 31Example 18 Compound Compound 6.54 50 3,475 6.95 blue 492 hr H45 42Example 19 Compound Compound 6.52 50 3,420 6.84 blue 468 hr H45 48Example 20 Compound Compound 6.53 50 3,505 7.01 blue 495 hr H45 55Example 21 Compound Compound 6.48 50 3,575 7.15 blue 490 hr H45 60Example 22 Compound Compound 6.53 50 3,325 6.65 blue 420 hr H60 14Example 23 Compound Compound 6.53 50 3,380 6.76 blue 399 hr H60 21Example 24 Compound Compound 6.54 50 3,430 6.86 blue 437 hr H60 42Example 25 Compound Compound 6.53 50 3,460 6.92 blue 445 hr H60 55Example 26 Compound Compound 6.48 50 3,510 7.02 blue 457 hr H60 60Example 27 Compound Compound 6.43 50 3,490 6.98 blue 453 hr H60 72Comparative ADN TPD 6.96 50 2,730 5.46 blue 248 hr Example 1 ComparativeH9 TPD 6.73 50 2,835 5.67 blue 384 hr Example 2

When a compound represented by Formula 1 according to embodiments of thepresent invention was used as a dopant in a blue emission layer,efficiency and lifespan of an organic light-emitting device may improvecompared to those of an organic light-emitting device using a relatedcompound as a blue dopant. In addition, when a compound represented byFormula 4 according to embodiments of the present invention is also usedat the same time as a host in the emission layer, this effect may befurther increased.

As described above, according to one or more embodiments of the presentinvention, the compound represented by Formula 1 has excellent stabilityand is suitable as an electron transporting material. An organiclight-emitting device using the compound of Formula 1 may have highefficiency, low voltage, high luminance, and long lifespan.

It should be understood that the exemplary embodiments described thereinshould be considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each exemplaryembodiment should typically be considered as available for other similarfeatures or aspects in other exemplary embodiments.

While one or more exemplary embodiments have been described withreference to the drawing, it will be understood by those of ordinaryskill in the art that various changes in form and details may be madetherein without departing from the spirit and scope as defined by thefollowing claims and equivalents thereof.

What is claimed is:
 1. A compound represented by Formula 1:

wherein in Formula 1, R₁ to R₈ and Ar₁ to Ar₄ are each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇); andat least one selected from Ar₁ to Ar₄ is represented by Formula 1-a:

wherein in Formula 1-a, R₁₁ is as defined in connection with R₁ to R₈; mis an integer selected from 1 to 7; * indicates a binding site; andwherein in Formulae 1 and 1-a, at least one of the substituents of thesubstituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀ alkoxy group,substituted C₃-C₁₀ cycloalkyl group, substituted C₂-C₁₀ heterocycloalkylgroup, substituted C₃-C₁₀ cycloalkenyl group, substituted C₂-C₁₀heterocycloalkenyl group, substituted C₆-C₆₀ aryl group, substitutedC₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthio group, substitutedC₁-C₆₀ heteroaryl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatic condensedheteropolycyclic group is selected from: a deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group,each substituted with at least one selected from a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoricacid or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇); a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group; aC₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and —N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);wherein Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ are eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.
 2. Thecompound of claim 1, wherein Ar₁ to Ar₄ in Formula 1 that are notrepresented by Formula 1-a are each independently selected from asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.3. The compound of claim 1, wherein in Formula 1, R₁ to R₈ are eachindependently selected from a hydrogen, a deuterium, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₆-C₆₀aryl group, and —Si(Q₃)(Q₄)(Q₅).
 4. The compound of claim 1, wherein Ar₁to Ar₄ in Formula 1 that are not represented by Formula 1-a are eachindependently a compound represented by any one of Formulae 2a to 2d:

wherein in Formulae 2a to 2d, Z₁ is selected from a hydrogen atom, adeuterium, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₆-C₂₀ aryl group, a substituted orunsubstituted C₁-C₂₀ heteroaryl group, a substituted or unsubstitutedC₆-C₂₀ condensed polycyclic group, a halogen group, a cyano group, anitro group, a hydroxyl group, and a carboxyl group; H₁ is selected from—O—, —S—, and —CR₅₁R₅₂—; p is an integer selected from 1 to 9; R₅₁ andR₅₂ are as defined in connection with R₁ to R₈; and * indicates abinding site.
 5. The compound of claim 1, wherein in Formula 1, R₂ andR₆ are each independently selected from a hydrogen, a deuterium, aC₁-C₂₀ alkyl group, a C₆-C₂₀ aryl group, and —Si(Q₄₁)(Q₄₂)(Q₄₃): whereinQ₄₁ to Q₄₃ are each independently selected from a C₁-C₆₀ alkyl group anda C₆-C₆₀ aryl group.
 6. The compound of claim 1, wherein in Formula 1,R₁, R₃ to R₅, R₇, and R₈ are each independently selected from a hydrogenand a deuterium.
 7. The compound of claim 1, wherein in Formula 1-a, R₁₁is selected from a hydrogen and a deuterium.
 8. The compound of claim 1,wherein the compound represented by Formula 1 is represented by any oneof Formulae 2 and 3:


9. The compound of claim 1, wherein the compound of Formula 1 isselected from compounds 1 through 72:


10. An organic light-emitting device comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerbetween the first electrode and the second electrode and comprising anemission layer, wherein the organic layer comprises the compoundrepresented by Formula 1 of claim
 1. 11. The organic light-emittingdevice of claim 10, wherein the first electrode is an anode, the secondelectrode is a cathode, and the organic layer comprises a hole transportregion between the first electrode and the emission layer, the holetransport region comprising at least one selected from a hole injectionlayer, a hole transport layer, and an electron blocking layer, and anelectron transport region between the emission layer and the secondelectrode, the electron transport region comprising at least oneselected from a hole blocking layer, an electron transport layer, and anelectron injection layer.
 12. The organic light-emitting device of claim10, wherein the emission layer comprises the compound represented byFormula
 1. 13. The organic light-emitting device of claim 10, whereinthe emission layer comprises the compound represented by Formula 1 as adopant.
 14. The organic light-emitting device of claim 10, wherein theemission layer further comprises a compound represented by Formula 4:

wherein in Formula 4, R₂₁ to R₃₆ are each independently selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇);wherein at least one of the substituents of the substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group isselected from: a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇); a C₃-C₁₀ cycloalkylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group; a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with at least oneselected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and —N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇),and wherein Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ are eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.
 15. Theorganic light-emitting device of claim 14, wherein the organiclight-emitting device comprises the compound represented by Formula 4 asa host.
 16. The organic light-emitting device of claim 14, wherein inFormula 4, R₂₅, R₂₇, R₃₁, R₃₂, and R₃₃ are each independently selectedfrom a hydrogen, a deuterium, a cyano group, a substituted orunsubstituted C₁-C₆₀ alkyl group, —Si(Q₃)(Q₄)(Q₅), and Formulae 3a to3c:

wherein in Formulae 3a to 3c, Z₁ is selected from a hydrogen atom, adeuterium, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₆-C₂₀ aryl group, a substituted orunsubstituted C₁-C₂₀ heteroaryl group, a substituted or unsubstitutedC₆-C₂₀ condensed polycyclic group, a halogen group, a cyano group, anitro group, a hydroxyl group, and a carboxyl group; H₁ is selected from—O—, —S—, —CR₅₁R₅₂—, and —NR₅₃—; p is an integer selected from 1 to 7;R₅₁ and R₅₃ are defined the same as R₂₁ to R₃₆, wherein, optionally, R₅₁and R₅₂ are linked to each other to form a ring; and * indicates abinding site.
 17. The organic light-emitting device of claim 14, whereinin Formula 4, R₂₁ to R₂₄, R₂₆, R₂₈ to R₃₀, R₃₄ to R₃₆ are eachindependently selected from a hydrogen and a deuterium.
 18. The organiclight-emitting device of claim 14, wherein the emission layer comprisesthe compound represented by Formula 1 as a fluorescent or phosphorescentdopant and the compound represented by Formula 4 as a fluorescent orphosphorescent host.
 19. The organic light-emitting device of claim 14,wherein the compound represented by Formula 4 is represented by one ofCompounds H1 to H78:


20. A flat panel display apparatus comprising the organic light-emittingdevice of claim 14, wherein the first electrode of the organiclight-emitting device is electrically connected to a source electrode ora drain electrode of a thin film transistor.